15,718

Caroline County, MD Homes

Section Image Section Image
  • 17 Greenridge Ave, Ridgely, MD 21660
    17 Greenridge Ave, Ridgely, MD 21660
    17 Greenridge Ave, Ridgely, MD 21660
    /16

    $265,000

    Sold Jul 31, 2025

    17 Greenridge Ave, Ridgely, MD 21660

    • 3 Beds
    • 1 Bath
    • 1,136 Sq Ft
    • Built 1991

    Last Sold Summary

    • $233/SF
    • 7 Days On Market

    Current Estimated Value $273,851

    Last Listing Agent Mary Mabry Keller Williams Select Realtors of Cambridge

    17 Greenridge Ave, Ridgely, MD 21660
    • 613 Denton Rd, Federalsburg, MD 21632
      613 Denton Rd, Federalsburg, MD 21632
      613 Denton Rd, Federalsburg, MD 21632
      /21

      Est $231,376

      Not Listed For Sale

      613 Denton Rd, Federalsburg, MD 21632

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1930
      613 Denton Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 1 Day On Market

  • 4757 Long Swamp Rd, Federalsburg, MD 21632
    4757 Long Swamp Rd, Federalsburg, MD 21632
    4757 Long Swamp Rd, Federalsburg, MD 21632
    /47

    $664,999

    • 4 Beds
    • 2.5 Baths
    • 2,576 Sq Ft

    4757 Long Swamp Rd, Federalsburg, MD 21632

    Welcome to 4757 Long Swamp Rd, a truly unique property in Federalsburg, MD, offering the perfect blend of equestrian facilities and comfortable country living on 7.04 acres. This well-maintained estate is ready for you and your horses, with no restrictions on property use and the added flexibility for the land to be subdivided. The grounds feature expansive pastures secured by electric fencing, a

    Billy Mister Keller Williams Realty

    4757 Long Swamp Rd, Federalsburg, MD 21632
  • 614 Market St, Denton, MD 21629
    614 Market St, Denton, MD 21629
    614 Market St, Denton, MD 21629
    /29

    $325,000

    Sold Oct 06, 2025

    614 Market St, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 2,508 Sq Ft
    • Built 1890

    Last Sold Summary

    • $130/SF
    • 53 Days On Market

    Current Estimated Value $319,316

    Last Listing Agent Michael Bozek Michael J. Bozek

    614 Market St, Denton, MD 21629
    • 510 Lincoln St, Denton, MD 21629
      510 Lincoln St, Denton, MD 21629
      510 Lincoln St, Denton, MD 21629
      /3

      Est $285,425

      Not Listed For Sale

      510 Lincoln St, Denton, MD 21629

      • Built 2024
      510 Lincoln St, Denton, MD 21629

      Last Sold Summary

      • 200 Days On Market

  • 1308 Chesapeake Dr, Denton, MD 21629
    1308 Chesapeake Dr, Denton, MD 21629
    1308 Chesapeake Dr, Denton, MD 21629
    /21

    $319,000

    $31K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft

    1308 Chesapeake Dr, Denton, MD 21629

    Well maintained ranch style home located in Cul -de -sac backing to trees. Three bedrooms ,two full baths , Eat in Kitchen, bright Living room plus den overlooking wooded back yard. Deck is ideal for that outdoor space to entertain. Two car garage offers space for storage in addition to parking. Sellers are offering allowance for new flooring. Make this your new home!

    Bonnie Johnson Keller Williams Realty

    1308 Chesapeake Dr, Denton, MD 21629
  • 12820 Porters Landing Rd, Greensboro, MD 21639
    12820 Porters Landing Rd, Greensboro, MD 21639
    /2

    $670,000

    Sold May 22, 2026

    12820 Porters Landing Rd, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 2,676 Sq Ft
    • Built 1989

    Last Sold Summary

    • 11% Below List Price
    • $250/SF
    • 86 Days On Market

    Current Estimated Value $722,781

    Last Listing Agent Penny Hollis Keller Williams Select Realtors of Annapolis

    12820 Porters Landing Rd, Greensboro, MD 21639
    • 13416 Greensboro Rd, Greensboro, MD 21639
      13416 Greensboro Rd, Greensboro, MD 21639
      13416 Greensboro Rd, Greensboro, MD 21639
      /26

      Est $147,991

      Not Listed For Sale

      13416 Greensboro Rd, Greensboro, MD 21639

      • Built 1971
      13416 Greensboro Rd, Greensboro, MD 21639

      Last Sold Summary

      • 71 Days On Market

  • 26471 Three Bridges Rd, Federalsburg, MD 21632
    26471 Three Bridges Rd, Federalsburg, MD 21632
    26471 Three Bridges Rd, Federalsburg, MD 21632
    /14

    $120,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 640 Sq Ft

    26471 Three Bridges Rd, Federalsburg, MD 21632

    **Back Active at no fault of the seller**Opportunity awaits at 26471 Three Bridges Rd in Federalsburg, MD! This partially remodeled 2-bedroom, 2-bath home is ready for your finishing touch. Inside, the property has been taken down to the framing and subflooring, giving you a true blank canvas to bring your vision to life—whether you’re an investor looking for your next project or a buyer ready to

    LEE MARLAND Keller Williams Realty

    26471 Three Bridges Rd, Federalsburg, MD 21632
  • 120 Parkland Rd, Greensboro, MD 21639
    120 Parkland Rd, Greensboro, MD 21639
    120 Parkland Rd, Greensboro, MD 21639
    /20

    $266,990

    Sold Oct 10, 2025

    120 Parkland Rd, Greensboro, MD 21639

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $252/SF
    • 24 Days On Market

    D.R. Horton Kinnamon Meadows

    120 Parkland Rd, Greensboro, MD 21639
    • 4845 Houston Branch Rd, Federalsburg, MD 21632
      4845 Houston Branch Rd, Federalsburg, MD 21632
      4845 Houston Branch Rd, Federalsburg, MD 21632
      /16

      Est $184,371

      Not Listed For Sale

      4845 Houston Branch Rd, Federalsburg, MD 21632

      4845 Houston Branch Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 91 Days On Market

  • 8590 Briar Patch Dr, Denton, MD 21629
    8590 Briar Patch Dr, Denton, MD 21629
    8590 Briar Patch Dr, Denton, MD 21629
    /7

    $527,000

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 2,942 Sq Ft

    8590 Briar Patch Dr, Denton, MD 21629

    Enjoy the space and privacy of this beautiful home situated on over 2 acres just outside of Denton. The main level features a formal dining room, a spacious primary suite with separate his-and-her closets, and a private bath with a walk-in shower. The kitchen opens to the family room, creating an inviting space for everyday living and entertaining.Custom window treatments enhance both the

    Barbara Blosser Long & Foster Real Estate, Inc.

    8590 Briar Patch Dr, Denton, MD 21629
  • 22650 Tanyard Rd, Preston, MD 21655
    22650 Tanyard Rd, Preston, MD 21655
    /2

    $348,000

    Sold Jun 03, 2026

    22650 Tanyard Rd, Preston, MD 21655

    • 3 Beds
    • 1 Bath
    • 1,160 Sq Ft
    • Built 1964

    Last Sold Summary

    • 7% Above List Price
    • $300/SF
    • 7 Days On Market

    Current Estimated Value $323,546

    Last Listing Agent Valerie Brown Coldwell Banker Realty

    22650 Tanyard Rd, Preston, MD 21655
    • 21994 Main St, Hillsboro, MD 21641
      21994 Main St, Hillsboro, MD 21641
      21994 Main St, Hillsboro, MD 21641
      /29

      Est $377,238

      Not Listed For Sale

      21994 Main St, Hillsboro, MD 21641

      • 3 Beds
      • 3 Baths
      • 4,000 Sq Ft
      • Built 1800
      21994 Main St, Hillsboro, MD 21641

      Last Sold Summary

      • 139 Days On Market

  • 103 Riverwalk Terrace, Federalsburg, MD 21632
    103 Riverwalk Terrace, Federalsburg, MD 21632
    103 Riverwalk Terrace, Federalsburg, MD 21632
    /21

    $229,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    103 Riverwalk Terrace, Federalsburg, MD 21632

    Hurry before it’s gone! This is an opportunity to buy in the sold out community of Riverwalk Terrace. The owner stayed at the home a few times some of the appliances never used. Open floor plan 1365 square feet , 3 bedrooms and 2.5 baths easy living. Only 2 years young this unit feels like new, was never a rental barley lived in. also backs up to the woods the private side of the community.

    Kat Thompson Benson & Mangold, LLC.

    103 Riverwalk Terrace, Federalsburg, MD 21632
  • 25999 Fox Grape Rd, Greensboro, MD 21639

    $379,000

    Sold Mar 20, 2026

    25999 Fox Grape Rd, Greensboro, MD 21639

    • 4 Beds
    • 2 Baths
    • 1,792 Sq Ft
    • Built 1987

    Last Sold Summary

    • $211/SF
    • 70 Days On Market

    Current Estimated Value $378,095

    Last Listing Agent Amy Betts Coldwell Banker Realty

    25999 Fox Grape Rd, Greensboro, MD 21639
    • 328 E Central Ave, Federalsburg, MD 21632
      328 E Central Ave, Federalsburg, MD 21632
      328 E Central Ave, Federalsburg, MD 21632
      /5

      Est $48,500

      Not Listed For Sale

      328 E Central Ave, Federalsburg, MD 21632

      328 E Central Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 28 Days On Market

  • 11142 Log Cabin Rd, Denton, MD 21629
    11142 Log Cabin Rd, Denton, MD 21629
    11142 Log Cabin Rd, Denton, MD 21629
    /55

    $635,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    11142 Log Cabin Rd, Denton, MD 21629

    Welcome to 11142 Log Cabin Road! This unique property offers the perfect combination of residential living and valuable commercial space, all on one expansive, 4.53 acre lot. This beautiful colonial-style home has great curb appeal with its classic look, neatly trimmed landscaping, and a spacious front yard shaded by mature trees. The main home spans over 2,700 square feet and features four

    Courtney Gallagher Keller Williams Realty Central-Delaware

    11142 Log Cabin Rd, Denton, MD 21629
  • 22490 Ash Blvd, Preston, MD 21655
    22490 Ash Blvd, Preston, MD 21655
    22490 Ash Blvd, Preston, MD 21655
    /46

    $348,000

    Sold Oct 14, 2025

    22490 Ash Blvd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 2001

    Last Sold Summary

    • $188/SF
    • 22 Days On Market

    Last Listing Agent Kathryn Tennant Douglas Realty, LLC

    22490 Ash Blvd, Preston, MD 21655
    • 26302 Sennett Rd, Denton, MD 21629
      26302 Sennett Rd, Denton, MD 21629
      26302 Sennett Rd, Denton, MD 21629
      /5

      Est $53,963

      Not Listed For Sale

      26302 Sennett Rd, Denton, MD 21629

      26302 Sennett Rd, Denton, MD 21629

      Last Sold Summary

      • 233 Days On Market

  • 107 Smith St, Federalsburg, MD 21632
    107 Smith St, Federalsburg, MD 21632
    107 Smith St, Federalsburg, MD 21632
    /22

    $184,000

    $5K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    107 Smith St, Federalsburg, MD 21632

    Move-In Ready & Beautifully Remodeled!This charming 3-bedroom, 1.5-bath home offers the perfect blend of comfort and convenience. Enjoy a spacious living room, separate dining area, and a dedicated laundry room for added functionality.The kitchen is designed for both everyday living and entertaining, featuring dual bar seating areas with open views to the living and dining spaces. One

    Dawn Hubbard Keller Williams Select Realtors of Cambridge

    107 Smith St, Federalsburg, MD 21632
  • 515 Vaughn Ave, Greensboro, MD 21639
    515 Vaughn Ave, Greensboro, MD 21639
    515 Vaughn Ave, Greensboro, MD 21639
    /35

    $239,900

    Sold Mar 31, 2026

    515 Vaughn Ave, Greensboro, MD 21639

    • 4 Beds
    • 2.5 Baths
    • 1,756 Sq Ft
    • Built 2004

    Last Sold Summary

    • 4% Below List Price
    • $137/SF
    • 27 Days On Market

    Current Estimated Value $242,531

    Last Listing Agent Chad Muse KD Realty Inc

    515 Vaughn Ave, Greensboro, MD 21639
    • 223 Old Denton Rd, Federalsburg, MD 21632
      223 Old Denton Rd, Federalsburg, MD 21632
      223 Old Denton Rd, Federalsburg, MD 21632
      /17

      Not Listed For Sale

      223 Old Denton Rd, Federalsburg, MD 21632

      • 3 Beds
      • 1 Bath
      • 1,488 Sq Ft
      • Built 1900
      223 Old Denton Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 53 Days On Market

  • 10819 Greensboro Rd, Denton, MD 21629
    10819 Greensboro Rd, Denton, MD 21629
    10819 Greensboro Rd, Denton, MD 21629
    /27

    $265,000

    • 2 Beds
    • 1 Bath
    • 1,092 Sq Ft

    10819 Greensboro Rd, Denton, MD 21629

    This home will be a Total Renovation in 2026. Consisting of 2 BR and 1 Bath. Situated on almost a half ac. Lovely back yard, and new Well, Septic has been inspected and is in acceptable working condition. Stones have been added to the driveway . A few more touches and it is move in ready. Don't wait to view this Newley redone home.

    Barbara Beaudet Brenton Realty Group

    10819 Greensboro Rd, Denton, MD 21629
  • 1105 Market St, Denton, MD 21629
    1105 Market St, Denton, MD 21629
    1105 Market St, Denton, MD 21629
    /29

    $261,000

    Sold Jan 13, 2026

    1105 Market St, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Built 2021

    Last Sold Summary

    • $201/SF
    • 85 Days On Market

    Current Estimated Value $268,334

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    1105 Market St, Denton, MD 21629
    • 0 Burnt Mill Rd Unit MDCM2005304, Ridgely, MD 21660
      0 Burnt Mill Rd Unit MDCM2005304, Ridgely, MD 21660
      0 Burnt Mill Rd Unit MDCM2005304, Ridgely, MD 21660
      /7

      Not Listed For Sale

      0 Burnt Mill Rd Unit MDCM2005304, Ridgely, MD 21660

      0 Burnt Mill Rd Unit MDCM2005304, Ridgely, MD 21660

      Last Sold Summary

  • 211 Bloomingdale Ave, Federalsburg, MD 21632
    211 Bloomingdale Ave, Federalsburg, MD 21632
    211 Bloomingdale Ave, Federalsburg, MD 21632
    /29

    $319,000

    $20K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 2,017 Sq Ft

    211 Bloomingdale Ave, Federalsburg, MD 21632

    Welcome to 211 Bloomingdale Ave. This custom‐built Brick Williamsburg‐style colonial showcases true craftsmanship, featuring beautiful hardwood floors throughout, custom built‐ins, and detailed moldings. The spacious living room offers an inviting wood‐burning fireplace, while the large great room with its vaulted ceiling provides flexible living space and could easily be converted into a third

    Jana Meredith Meredith Fine Properties

    211 Bloomingdale Ave, Federalsburg, MD 21632
  • 334 Deep Shore Rd, Denton, MD 21629
    334 Deep Shore Rd, Denton, MD 21629
    334 Deep Shore Rd, Denton, MD 21629
    /48

    $350,000

    Sold Jan 14, 2026

    334 Deep Shore Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,640 Sq Ft
    • Built 1957

    Last Sold Summary

    • $213/SF
    • 15 Days On Market

    Current Estimated Value $343,792

    Last Listing Agent Laura Anthony Benson & Mangold, LLC

    334 Deep Shore Rd, Denton, MD 21629
    • 0 Burnt Mill Rd Unit MDCM2005302, Ridgely, MD 21660
      0 Burnt Mill Rd Unit MDCM2005302, Ridgely, MD 21660
      0 Burnt Mill Rd Unit MDCM2005302, Ridgely, MD 21660
      /7

      Not Listed For Sale

      0 Burnt Mill Rd Unit MDCM2005302, Ridgely, MD 21660

      0 Burnt Mill Rd Unit MDCM2005302, Ridgely, MD 21660

      Last Sold Summary

  • 205 Park Ave, Federalsburg, MD 21632
    205 Park Ave, Federalsburg, MD 21632
    205 Park Ave, Federalsburg, MD 21632
    /8

    $239,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    205 Park Ave, Federalsburg, MD 21632

    **Construction has not yet began, please feel free to drive by the lot. Completion will be for this August 2026!!*** The photos provided in the MLS are for reference purposes only and are intended to reflect the style and quality of similar fixtures, finishes, and features. Actual materials, fixtures, finishes, and selections may vary based on builder availability and final specifications.

    Erene Katris Coldwell Banker Realty

    205 Park Ave, Federalsburg, MD 21632
  • 124 Julie Ln, Federalsburg, MD 21632
    124 Julie Ln, Federalsburg, MD 21632
    124 Julie Ln, Federalsburg, MD 21632
    /28

    $233,990

    Sold Aug 20, 2025

    124 Julie Ln, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $171/SF
    • 20 Days On Market

    124 Julie Ln, Federalsburg, MD 21632
    • 20735 Tammuxzena Dr, Preston, MD 21655
      20735 Tammuxzena Dr, Preston, MD 21655
      20735 Tammuxzena Dr, Preston, MD 21655
      /63

      Est $552,952

      Not Listed For Sale

      20735 Tammuxzena Dr, Preston, MD 21655

      • 3 Beds
      • 2.5 Baths
      • 2,250 Sq Ft
      • Built 2025
      20735 Tammuxzena Dr, Preston, MD 21655

      Last Sold Summary

      • 6 Days On Market

  • 504 Sunset Blvd, Ridgely, MD 21660
    504 Sunset Blvd, Ridgely, MD 21660
    504 Sunset Blvd, Ridgely, MD 21660
    /30

    $280,000

    • 3 Beds
    • 1 Bath
    • 864 Sq Ft

    504 Sunset Blvd, Ridgely, MD 21660

    This delightful 3-bedroom bungalow offers a perfect blend of comfort and community. Built in 1940, this home exudes character with its sturdy block construction and inviting layout. The cozy 864 sq. ft. interior is complemented by essential appliances, including a refrigerator, stove, washer, and dryer, making daily living a breeze. The generous half-acre lot provides ample outdoor space for

    Cheryl Knotts Chesapeake Real Estate Associates, LLC

    504 Sunset Blvd, Ridgely, MD 21660
  • 24029 Meadows Dr, Ridgely, MD 21660
    24029 Meadows Dr, Ridgely, MD 21660
    24029 Meadows Dr, Ridgely, MD 21660
    /39

    $365,000

    Sold Mar 27, 2026

    24029 Meadows Dr, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft
    • Built 1990

    Last Sold Summary

    • $204/SF
    • 67 Days On Market

    Current Estimated Value $376,106

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    24029 Meadows Dr, Ridgely, MD 21660
    • 0 Bridgetown Rd Unit MDCM2005246, Goldsboro, MD 21636
      0 Bridgetown Rd Unit MDCM2005246, Goldsboro, MD 21636
      0 Bridgetown Rd Unit MDCM2005246, Goldsboro, MD 21636
      /4

      Not Listed For Sale

      0 Bridgetown Rd Unit MDCM2005246, Goldsboro, MD 21636

      0 Bridgetown Rd Unit MDCM2005246, Goldsboro, MD 21636

      Last Sold Summary

      • 11 Days On Market

  • 0 Charlotte Ave, Federalsburg, MD 21632
    0 Charlotte Ave, Federalsburg, MD 21632
    /2

    $27,500

    • Land
    • 12,196 Sq Ft
    • $98,214 per Acre

    0 Charlotte Ave, Federalsburg, MD 21632

    Build your dream home in the heart of Federalsburg! This approximately 0.28-acre residential lot is located within town limits and is zoned R-1 Single Family Residential. Public water and public sewer are available, offering a great opportunity for new construction in an established community. Conveniently located near local parks, schools, shopping, dining, and major commuter routes. Whether

    Heather Brummell Keller Williams Realty

    0 Charlotte Ave, Federalsburg, MD 21632
  • 124 Parkland Rd, Greensboro, MD 21639
    124 Parkland Rd, Greensboro, MD 21639
    124 Parkland Rd, Greensboro, MD 21639
    /20

    $267,490

    Sold Aug 12, 2025

    124 Parkland Rd, Greensboro, MD 21639

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $253/SF
    • 6 Days On Market

    D.R. Horton Kinnamon Meadows

    124 Parkland Rd, Greensboro, MD 21639
    • 125 Riverwalk Terrace, Federalsburg, MD 21632
      125 Riverwalk Terrace, Federalsburg, MD 21632
      125 Riverwalk Terrace, Federalsburg, MD 21632
      /28

      Est $235,209

      Not Listed For Sale

      125 Riverwalk Terrace, Federalsburg, MD 21632

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft
      • Built 2024
      125 Riverwalk Terrace, Federalsburg, MD 21632

      Last Sold Summary

      • 42 Days On Market

  • Lot 1 E Sunset Ave, Greensboro, MD 21639
    Lot 1 E Sunset Ave, Greensboro, MD 21639
    Lot 1 E Sunset Ave, Greensboro, MD 21639
    /8

    $79,900

    Pending
    • Land
    • 4.31 Acres
    • $18,538 per Acre

    Lot 1 E Sunset Ave, Greensboro, MD 21639

    Large wooded lot on the outside of town. Perc approved for a 2' mound system. Located at the corner of Sunset Ave and River Rds. 4.3 acres Some forest conservation area. Only four lots in this subdivision and only three lots available.

    Marcia Rostien Long & Foster Real Estate, Inc.

    Lot 1 E Sunset Ave, Greensboro, MD 21639
  • 3471 Laurel Grove Rd, Federalsburg, MD 21632
    3471 Laurel Grove Rd, Federalsburg, MD 21632
    /2

    $100,000

    Sold Feb 20, 2026

    3471 Laurel Grove Rd, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 888 Sq Ft
    • Built 1965

    Last Sold Summary

    • 9% Below List Price
    • $113/SF
    • 31 Days On Market

    Current Estimated Value $148,000

    Last Listing Agent Heather Brummell Keller Williams Realty

    3471 Laurel Grove Rd, Federalsburg, MD 21632

Showing Results 121 - 160, Page 4 of 18

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